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[摘要]:The synthesis and characterization of the first di-beta-naphthyl-substituted pyrylogens, N-methyl-2,6-di-beta-naphthyl-4,4'-pyrylogen bis(tetrafluoroborate) and N-methyl-2,6-di-beta-naphthyl-4,2'-pyrylogen bis(tetrafluoroborate) are reported. The photophysical and electrochemical behaviors of these new pyrylogens are examined and compared to the previously reported diphenyl-substituted analogs, N-methyl-2,6-diphenyl-4,4'-pyrylogen bis(tetrafluoroborate) and N-methyl-2,6-diphenyl-4,2'-pyrylogen bis(tetrafluoroborate) as well as to 2,4,6-triphenylpyrylium tetrafluoroborate, the typical electron-transfer photocatalyst. The newly synthesized pyrylogens exhibit substantially lower excitation energies. The results are supported by theoretical calculations using the B3LYP/6-31G(d) and time-dependent DFT (TD-DFT) CAM-B3LYP/6-31G(d) computational models. In addition, insight into the reduction reactions of the new pyrylogens to their radical cation and neutral redox partners is also provided. |
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